Diisopropylethylamine → N'-(6-chloropyridazin-3-yl)-2-(quinolin-6-yl)propanehydrazide

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 2-(quinolin-6-yl)propanoic acid (3260 mg, 16201 μmol) and DIEA (2830 μl, 16201 μmol) in DMF (25 mL) was added o-(7-azabenzotriazol-1-yl)-n,n,n′,n-tetramethyl uronium hexafluorophosphate (6160 mg, 16201 μmol) whole at 23° C. under nitrogen. The solution was stirred for 60 min, cooled to 0° C., then added 1-(6-chloropyridazin-3-yl)hydrazine (2342 mg, 16201 μmol). After 20 h stirring at 23° C., the reaction was then partitioned between 9:1 CHCl3/IPA (100 mL) and 5% NaHCO3 (50 mL). The organic phase was then dried over MgSO4, concentrated to an oil, then purified on silica (120 g) eluting with 0>10% of 2 M NH3 in MeOH/DCM. The product was isolated as an off white solid. MS (ESI pos. ion) m/z: 328 (MH+). Calc'd exact mass for C16H14ClN5O: 327.

Provenance & Evidence